SMILES in QSPR/QSAR modeling: Results and perspectives

Andrey A. Toropov; Emilio Benfenati

doi:10.2174/157016307781483432

SMILES in QSPR/QSAR modeling: Results and perspectives

Andrey A. Toropov, Emilio Benfenati

Istituto di Ricerche Farmacologiche "Mario Negri"

Research output: Contribution to journal › Article › peer-review

Abstract

The technique of constructing optimal descriptors calculated with the Simplified molecular input line entry system (SMILES) is described. SMILES based optimal descriptors and descriptors calculated with molecular graphs (hydrogen filled graphs and graph of atomic orbitals) are compared in modeling done by means of quantitative structure - property/activity relationships (QSPR/QSAR). QSPR/QSAR models for normal boiling points of organic compounds, mutagenicity of heteroaromatic amines, toxicity, and anti-HIV-1 potentials of TIBO and HEPT derivatives are described in details. Possible ways to improve the SMILES based concept of QSPR/QSAR analyses are discussed.

Original language	English
Pages (from-to)	77-116
Number of pages	40
Journal	Current Drug Discovery Technologies
Volume	4
Issue number	2
DOIs	https://doi.org/10.2174/157016307781483432
Publication status	Published - Aug 2007

Keywords

Optimal descriptor
QSPR/QSAR
SMILES

ASJC Scopus subject areas

Drug Discovery

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abstract = "The technique of constructing optimal descriptors calculated with the Simplified molecular input line entry system (SMILES) is described. SMILES based optimal descriptors and descriptors calculated with molecular graphs (hydrogen filled graphs and graph of atomic orbitals) are compared in modeling done by means of quantitative structure - property/activity relationships (QSPR/QSAR). QSPR/QSAR models for normal boiling points of organic compounds, mutagenicity of heteroaromatic amines, toxicity, and anti-HIV-1 potentials of TIBO and HEPT derivatives are described in details. Possible ways to improve the SMILES based concept of QSPR/QSAR analyses are discussed.",

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